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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
PTIO is an NO scavenger that reacts with NO to form corresponding imino nitrogen oxides and •NO2.
Synonyms: α-Phenyltetramethylnitronyl nitroxide
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| CAS No. : | 18390-00-6 |
| Formula : | C13H17N2O2 |
| M.W : | 233.29 |
| SMILES Code : | CC1(N(C(C2=CC=CC=C2)=[N+](C1(C)C)[O-])[O])C |
| Synonyms : |
α-Phenyltetramethylnitronyl nitroxide
|
| English Name : | 2-Phenyl-4,4,5,5-tetramethylimidazoline-1-oxyl 3-oxide |
| MDL No. : | MFCD00059929 |
| InChI Key : | DYUUGILMVYJEHY-UHFFFAOYSA-N |
| Pubchem ID : | 2733513 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 87% | With hydrogenchloride; sodium nitrite In 1,4-dioxane for 0.25h; Ambient temperature; | |
| 79% | With hydrogenchloride; sodium nitrite In methanol at 20℃; for 1h; | |
| 57% | With 2,3,5,6-tetrafluoro-7,7',8,8'-tetracyanoquinodimethane In acetonitrile for 0.0333333h; |
| With nitric oxide In hexane; chloroform at 14.9℃; | ||
| With N-(2-butyl-1,3-dioxo-2,3-dihydro-1H-benzo[de]isoquinolin-6-yl)N-methylnitrosoamine In aq. phosphate buffer; dimethyl sulfoxide | ||
| With hydrogenchloride; toluene-4-sulfonic acid; sodium nitrite In dichloromethane; water | ||
| With sodium nitroprusside In water for 24h; Sonication; | ||
| With C32H33N5O6 In aq. phosphate buffer; ethanol; dimethyl sulfoxide Irradiation; | ||
| UV-irradiation; |

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 60% | With hydrogenchloride; zinc at 100℃; for 1.5h; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 73% | With iron; acetic acid for 1h; Ambient temperature; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 51% | With sodium tungstate; dihydrogen peroxide In methanol for 48h; Ambient temperature; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 1: 78% 2: 12% | Stage #1: 2-Phenyl-4,4,5,5-tetramethylimidazolidine With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid In dichloromethane for 1h; Ice cooling; Stage #2: With sodium periodate In dichloromethane Further stages.; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Stage #1: 2-phenyl-4,4,5,5-tetramethylimidazolin-3-oxide-1-oxyl With hexamethylenetetramine In methanol at 20℃; Stage #2: With lead dioxide In methanol for 1h; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 47% | In ethanol at 0℃; for 24h; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 85% | With sodium periodate In chloroform; water at 0 - 20℃; | |
| 80% | With lead dioxide In methanol at 20℃; for 3h; | |
| 80% | With lead dioxide In methanol at 20℃; for 0.333333h; |
| 80% | With lead dioxide In methanol at 20℃; for 0.5h; | |
| With sodium periodate; sodium hydrogencarbonate In dichloromethane; water Cooling with ice; |

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 3 steps 1: 79 percent / Al/Hg / tetrahydrofuran; H2O / 0.75 h / -7 - -2 °C 2: 96 percent / p-TsOH*H2O / methanol / 48 h / 20 °C 3: 85 percent / NaIO4 / CHCl3; H2O / 0 - 20 °C | ||
| Multi-step reaction with 3 steps 1: 63 percent / Zn; NH4Cl / tetrahydrofuran; H2O / 3 h / 10 °C 2: 85 percent / methanol / 16 h / 20 °C 3: 80 percent / lead dioxide / methanol / 0.33 h / 20 °C | ||
| Multi-step reaction with 3 steps 1: 63 percent / Zn; NH4Cl / tetrahydrofuran; H2O / 19 h / 4 - 10 °C 2: 85 percent / methanol / 1 h / 20 °C 3: 80 percent / lead dioxide / methanol / 3 h / 20 °C |
| Multi-step reaction with 3 steps 1.1: 81 percent / Sn; aq. HCl / 3 h / Heating 2.1: 78 percent / aq. H2SO4 / methanol / 1 h / 20 °C / pH 3 - 4 3.1: m-chloroperbenzoic acid; NaHCO3 / CH2Cl2 / 1 h / Ice cooling 3.2: 78 percent / aq. NaIO4 / CH2Cl2 | ||
| Multi-step reaction with 3 steps 1.1: 81 percent / Sn; aq. HCl / 3 h / Heating 2.1: 99 percent / diethyl ether / ice cooling 3.1: m-chloroperbenzoic acid; NaHCO3 / CH2Cl2 / 1 h / Ice cooling 3.2: 78 percent / aq. NaIO4 / CH2Cl2 | ||
| Multi-step reaction with 3 steps 1: zinc; ammonium chloride / water; tetrahydrofuran / 10 - 12 °C 2: toluene-4-sulfonic acid / methanol / 120 h / 20 °C / Schlenk technique; Inert atmosphere 3: sodium hydrogencarbonate; sodium periodate / dichloromethane; water / Cooling with ice | ||
| Multi-step reaction with 5 steps 1.1: ammonium chloride; zinc; cadmium(II) sulfate octahydrate / tetrahydrofuran; water / 2 h / Cooling with ice 2.1: water / 0.08 h / 20 °C 3.1: sodium periodate / water; ethyl acetate / 0 °C 4.1: tetrahydrofuran / 1 h / 110 °C / Microwave irradiation; Sealed tube 4.2: 0.33 h 5.1: 1,3,5,7-tetramethyl-6-phenyl-2,4,8-trioxa-6-phosphaadamantane; tris(dibenzylideneacetone)dipalladium(0) chloroform complex / toluene / 0.33 h / 20 °C / Inert atmosphere |

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 2 steps 1: 96 percent / p-TsOH*H2O / methanol / 48 h / 20 °C 2: 85 percent / NaIO4 / CHCl3; H2O / 0 - 20 °C | ||
| Multi-step reaction with 2 steps 1: 85 percent / methanol / 16 h / 20 °C 2: 80 percent / lead dioxide / methanol / 0.33 h / 20 °C | ||
| Multi-step reaction with 2 steps 1: 85 percent / methanol / 1 h / 20 °C 2: 80 percent / lead dioxide / methanol / 3 h / 20 °C |
| Multi-step reaction with 2 steps 1: toluene-4-sulfonic acid / methanol / 120 h / 20 °C / Schlenk technique; Inert atmosphere 2: sodium hydrogencarbonate; sodium periodate / dichloromethane; water / Cooling with ice | ||
| Multi-step reaction with 4 steps 1.1: water / 0.08 h / 20 °C 2.1: sodium periodate / water; ethyl acetate / 0 °C 3.1: tetrahydrofuran / 1 h / 110 °C / Microwave irradiation; Sealed tube 3.2: 0.33 h 4.1: 1,3,5,7-tetramethyl-6-phenyl-2,4,8-trioxa-6-phosphaadamantane; tris(dibenzylideneacetone)dipalladium(0) chloroform complex / toluene / 0.33 h / 20 °C / Inert atmosphere |

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 2 steps 1.1: 78 percent / aq. H2SO4 / methanol / 1 h / 20 °C / pH 3 - 4 2.1: m-chloroperbenzoic acid; NaHCO3 / CH2Cl2 / 1 h / Ice cooling 2.2: 78 percent / aq. NaIO4 / CH2Cl2 | ||
| Multi-step reaction with 2 steps 1.1: 99 percent / diethyl ether / ice cooling 2.1: m-chloroperbenzoic acid; NaHCO3 / CH2Cl2 / 1 h / Ice cooling 2.2: 78 percent / aq. NaIO4 / CH2Cl2 |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 66% | In diethyl ether Cu(CF3COO)2*xH2O was added to soln. NITPh in ether; heptane was added, soln. was concd. and cooled to -18°C; elem. anal.; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 78% | In benzene Ar-atmosphere; slight excess ligand, stirring at room temp. overnight (pptn.); collection (filtration), washing (C6H6), drying (vac., 80°C); elem. anal.; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 73% | In dichloromethane soln. of Hg-complex in CH2Cl2 mixed with soln. of ligand in CH2Cl2; evapd. of solvent, washed with hexane and CH2Cl2; elem. anal.; |